Cycling shorts...what's underneath?

I'm very new to cycling, and just bought my first water bottle and Jersey yesterday. Clearly the gym shorts I wore over my cycling shorts on my last ride were an impediment. But are you supposed to ride nude underneath? Just want to understand how to dress to avoid getting in my own way. Thanks

The pad ("chamois") in bike shorts has fairly soft foam which fully compresses easily when you sit on the saddle. Because of this it provides little in the way of cushioning, but what it does do is add body and stiffness to the fabric of the shorts so that it doesn't bunch up or wad in the folds of your skin and cause chafing. Putting underwear between the pad and you butt defeats this.

The chamois should also wick moisture away from your soft sensitive bits more easily and again cotton undies defeat this. Also, the location of many types of underwear leads to chafing with just the elastic bands at the leg holes.

Punctuation is important. It's the difference between "I helped my uncle, Jack, off a horse" and "I helped my uncle Jack off a horse"

Yea nothing, they are your underwear. I wear basketball shorts over my cycle shorts too, how is this an impediment? Is it the seam? In do 50 mile rides regularly like this and doesnt bother me.

For one you look like you have something to hide.
The wind would bug the heck out of me. Here it is windy 3/4 of the year.
For me I have worked my arse off for years and have no desire to hide in baggy clothes. Heck when I weighed over 200lbs I wore lycra. Shame is for kids.

one of the benefits of the pad is to soak up sweat and keep it off your body, so cotton undies will be pointless.
Wicking polyester undies perform the same sweat removal function as the pad, so if you want to wear the same bike shorts for 2-3 rides before needing to wash them then you could try using that.

Until you catch the back waistband of your gym shorts on the nose of your saddle and then get caught. If you're coming up at a light, it can suck because you're in traffic and the best way is to stop and put one foot back on the ground and then start over.

Punctuation is important. It's the difference between "I helped my uncle, Jack, off a horse" and "I helped my uncle Jack off a horse"